Cesium carbonate → 6-Bromo-1-(3-cyclopropoxypropyl)-3,3-dimethylindolin-2-one

HRID 1507590Notes

Reaction equation

HRID 1507590 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:13])([CH3:12])[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:21][CH2:22][CH2:23][O:24][CH:25]1[CH2:27][CH2:26]1>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:13])([CH3:12])[C:7](=[O:11])[N:8]2[CH2:21][CH2:22][CH2:23][O:24][CH:25]2[CH2:27][CH2:26]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 106576496-bromo-3,3-dimethyl-2,3-dihydro-1H-indol-2-oneHCID 90046503(3-Bromopropoxy)cyclopropane

Product 1

HCID 900463506-Bromo-1-(3-cyclopropoxypropyl)-3,3-dimethylindolin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

To a suspension of 6-bromo-3,3-dimethylindolin-2-one (example 14a, 300 mg, 1.25 mmol) and Cs2CO3 (814 mg, 2.5 mmol) in DMF (2 ml) was added a solution of (3-bromopropoxy)cyclopropane (447 mg, 2.5 mmol) in DMF (0.5 ml). The reaction mixture was heated to 70° C. for 3 hours. The reaction mixture was filtered through sintered glass and concentrated. The crude material was purified by flash chromatography on silica gel using ethyl acetate as eluent. The title compound was obtained as orange viscous oil (360 mg).

Workup

  1. filtrationThe reaction mixture was filtered through sintered glass
  2. concentrationconcentrated
  3. customThe crude material was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-eeb776ded8f2482daf1f5e5d5b8d17e0
Source dataset
uspto-grants-2015_12
Patent number
US09221816B2

Reaction notes

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